Department of Chemistry and Biochemistry , University of California , Los Angeles , California 90095-1569 , United States.
Chemical Development , Boehringer Ingelheim Pharmaceuticals, Inc. , 900 Ridgebury Road , Ridgefield , Connecticut 06877-0368 , United States.
Org Lett. 2020 Feb 21;22(4):1665-1669. doi: 10.1021/acs.orglett.0c00267. Epub 2020 Feb 4.
Silyl triflate precursors to benzyne and related intermediates have emerged as valuable synthetic building blocks. However, data addressing the safety of employing these silyl triflate precursors are lacking. We report the calorimetric analysis of a typical Kobayashi procedure for forming and trapping benzyne using a silyl triflate precursor. Our findings suggest that, unlike benzenediazonium carboxylate precursors to benzyne, silyl triflates may be employed under mild conditions without severe concern for runaway reaction.
硅基三氟甲磺酸酯前体作为有价值的合成砌块，已经在苯炔和相关中间体的合成中崭露头角。然而，目前缺乏关于使用这些硅基三氟甲磺酸酯前体的安全性数据。我们报告了使用硅基三氟甲磺酸酯前体制备和捕获苯炔的典型小林（Kobayashi）反应的量热分析。我们的研究结果表明，与苯并二氮唑羧酸前体不同，硅基三氟甲磺酸酯在温和条件下使用时，不会产生严重的失控反应，可以不必过于担心。
